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Piperidine → 4-[1-(2-aminopyrimidin-4-yl)-3-methyl-1H-indazol-6-yl]-2-(1,3-oxazol-4-yl)but-3-yn-2-ol

HRID 1398552
ノート
印刷プレビュー

反応式

HRID 1398552 の反応式
I[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:18])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)=[CH:4][CH:3]=1.N1CCCCC1.[O:25]1[CH:29]=[C:28]([C:30]([OH:34])([C:32]#[CH:33])[CH3:31])[N:27]=[CH:26]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[NH2:17][C:13]1[N:12]=[C:11]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([C:33]#[C:32][C:30]([C:28]4[N:27]=[CH:26][O:25][CH:29]=4)([OH:34])[CH3:31])[CH:10]=3)[C:6]([CH3:18])=[N:7]2)[CH:16]=[CH:15][N:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8082PiperidineHCID 681816364-(6-Iodo-3-methylindazol-1-yl)pyrimidin-2-amineHCID 866695772-(1,3-Oxazol-4-yl)but-3-yn-2-ol

生成物 1

HCID 601651414-[1-(2-aminopyrimidin-4-yl)-3-methyl-1H-indazol-6-yl]-2-(1,3-oxazol-4-yl)but-3-yn-2-ol

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418397
HCID 178418397、化合物
触媒

実験手順

To a vial was added 4-(6-iodo-3-methylindazol-1-yl)pyrimidin-2-amine (150 mg, 0.43 mmol), piperidine (1.5 mL), tetrakis(triphenylphosphine)palladium (49.36 mg, 0.04 mmol), copper(I) iodide (8.14 mg, 0.04 mmol) and 2-(1,3-oxazol-4-yl)but-3-yn-2-ol (87.87 mg, 0.64 mmol). The mixture was stirred at RT for 20 mins. Reaction mixture was concentrated in vacuo. DCM (5 mL) added and mixture was concentrated in vacuo. This was repeated twice. The crude material was purified by column chromatography (Biotage, 98:2 to 88:12 DCM: methanol gradient). Further purification by flash column chromatography gave the title compound: 1H (500 MHz, DMSO) delta 1.81 (3H, s), 2.58 (3H, s), 6.26 (1H, s), 6.99 (2H, s), 7.04 (1H, d, J=5.5 Hz), 7.39 (1H, dd, J=8.2, 1.1 Hz), 7.85 (1H, d, J=8.1 Hz), 8.13 (1H, s), 8.26 (1H, d, J=5.5 Hz), 8.36 (1H, s), 8.87 (1H, s); LC-MS: m/z=+361.05 (M+H)+.

後処理

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionDCM (5 mL) added
  4. concentrationmixture was concentrated in vacuo
  5. customThe crude material was purified by column chromatography (Biotage, 98:2 to 88:12 DCM: methanol gradient)
  6. customFurther purification by flash column chromatography

出典と根拠

ORDレコード
ord-a7a66913ddce41cf929e4c3f0c892eb9
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901313B2

反応ノート

読み込み中…

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